"Chemical ligation": a versatile method for nucleoside modification with boron clusters.
A general approach to the synthesis of nucleoside conjugates containing carborane and metallocarborane complexes, based on Huisgen 1,3-dipolar cycloaddition ("chemical ligation"), is described. Boron-cluster-donors bearing terminal azide or ethynyl groups were prepared in the ring-opening reaction of dioxane-boron-cluster adducts and an azide anion or suitable alkynol-derived alcoholate nucleophile. Analogous derivatives bearing terminal sulfhydryl groups were also prepared. Nucleosides with various spacers containing terminal azide or ethynyl groups, located within nucleobases or sugar residues, were used as boron-cluster acceptors. The proposed methodology provides a convenient way to synthesize libraries of boron-cluster-modified nucleosides for various applications.
Wojtczak
Błazej A
BA
Institute of Medical Biology, Laboratory of Molecular Virology and Biological Chemistry, Polish Academy of Sciences, 106 Lodowa St. 93-232 Lodz, Poland.
Andrysiak
Agnieszka
A
Grüner
Bohumír
B
Lesnikowski
Zbigniew J
ZJ
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D001896:Boron Compounds; D009705:Nucleosides